What Could Have Been
by MrsBigTuna
Summary: Five times Rory and Jess could have met. Slight AU. Literati oneshot.


_**Disclaimer: I don't Gilmore Girls. Any copyright infringements are unintentional. In other words, I don't blip. **_

_Summary: Five times Rory and Jess could have met. Most of this is AU. Literati oneshot. _

_A/N: I've never wrote anything in this fandom. So yeah, shooting in the dark here. Hope you enjoy and reviews are always love. _

* * *

_October 2000_

"I can't believe you actually dragged me out of school for this." Rory was walking alongside her mother, passing by small store fronts, carrying several shopping bags.

Lorelei chuckled as the turned another corner, which was littered with more pedestrians spilling from the dirty building that made up Greenwich Village. "Oh come on, any kid would be thrilled to pulled out of school for a day of fun in New York. I swear, I have to remember your mine."

Rory shook her head when she saw a hot dog vendor at the end of the block. "Ooh, food!"

Lorelei nodded as she caught to her daughter. "Oh, she's mine." As she bought two hot dogs, she noticed a small, obscure used record store. Yanking Rory from the cart, she hurried over the vinyl haven. Lorelei sniffed the air, smiling. "Smell that, kid? _That_ my child, is the smell of music, conveniently packaged in a bit of plastic." She pushed Rory forward. "Don't come back with anything less than three CDs." She watched Rory laugh, heading toward the back as she went straight for the classic rock section.

Rory wondered over to the alt rock section, busing herself as she perused some David Bowie. While she was looking over an EP of _Ashes to Ashes_, she looked up to find another patron. She wouldn't have paid him much attention, but the fact that he seemed closer to her age, possibly was her age left her intrigued. _Was he ditching class too?_ She swept her eyes, seeing no parental guardian, figuring he indeed was skipping class. She looked back down, considering the CD when she heard the boy scoff. She looked up alarmed, seeing him looking past her to the next aisle over. She surreptitiously turned to see what had offended him, discovering a middle aged man lingering near a display for Britney Spears' latest album. Giggling, Rory turned back to the boy with a cigarette behind his ear, sharing a small but strangely familiar smirk.

Fingering Depeche Mode, she wasn't aware that the boy had moved until he was nearly shoulder to shoulder to her, perusing The Clash. Nodding approvingly, she moved over to Cocteau Twins fondly, whom she had always felt sentimental for the use of her name for one of their songs. Unintentionally, she bumped into him, facing the boy. Although the eye contact was brief, she found herself smile once again. The boy smirked at her timid demeanor, reaching past her for an old Blur album. He walked around her to scrutinize it more, leaving Rory at the end of the aisle alone. She tucked a strand of hair behind her ear, trying to brush weird boy away when he appeared by her side again. "Hey."

Rory had picked up another album, briefly seeing that it was Death Cab for Cutie, she didn't tense up as much. Holding back another smile, she quietly spoke. "Hi." She tapped lightly over her pile of plastic, avoiding his eyes. She looked up at his shirt, another giggle stifled as the brilliantly colored Metallica logo stood straight ahead. "Cool shirt."

The boy looked down with a shrug. "Thanks." Seemingly sizing her up, he tried to peek at her stash. "What did you finally settle with?"

A dangerous red blush crept up her neck as she stammered. "Um, well... I got the new--"

"Come on, kiddo. We gotta go!" Lorelei waved for Rory at the front of the store, holding a bag that seemed to be stuffed with vinyl.

Rory inwardly cursed her mother, walking at a snails pace to join her. She turned quickly, seeing the boy wave as he went back to the CDs, leaving Rory feeling shortchanged and to wonder on the way home about the nameless Metallica fan.

* * *

_April 2004_

"Tell me why we're here again?" Rory crossed her arms, bracing herself in the unseasonably cool evening, peeking toward the front of the crowd. She had felt better earlier about the impromptu trip to New York City to see Beck at Madison Square Garden after one of the reporters on the paper had encouraged everyone to go after his cousins had scored an entire row. She fidgeted slightly, as the nagging feeling of leaving her studying to the wayside reared its ugly head. "Maybe this wasn't such a good idea."

Paris, who was tapping her feet impatiently, turned to Rory in exasperation. "Would you relax, Gilmore. We're supposed to be a little reckless every now and than."

Rory stifled a chuckle, hearing Paris Gellar telling her to relax. "I suppose you're right."

Paris smirked. "Aren't I always." Rory knew that she meant that as a statement, rolling her eyes. Paris shook her head, pushing people out of the way to get to the head of the line. "Is it too much to ask to find someone capable of doing more than removing the sticky from the blue strap, geez!" She continued to push past, disregarding the parade of nasty commoners displaying crude hand gestures.

Rory leaned against the building, looking ahead at the passerby. She blinked when she noticed someone staring back. He wasn't out of place as she seemed to feel amongst the crowd with the cigarette in his mouth, standing by the lightpost. He smirked at her, causing an innate reaction to blush. She turned quickly, finding Glenn standing near. "Hey, Glenn."

Glenn turned alarmed, smiling easily when he saw Rory. "Hey." There still seemed to be some awkwardness between them since her and Paris unceremoniously departure on Spring Break, leaving him and the rest of their group to fend for themselves. "I can't believe we're going to see Beck." He smiled sincerely than, putting Rory at ease.

"Yeah, I know. I've always wanted to see him live. I hear he's great." She tried not to pay attention to the guy across the way, who hadn't stopped looking at her, but attempted to not seem affected. Before Rory got to say another word, Paris was motioning for her and Glenn to join her at the front. She pulled Glenn along, seeing the rest of their group being escorted inside.

Just as Rory was about to enter, she noticed that the smoking guy had left his post. She shrugged it off, smiling as Paris pushed back someone trying to sneak in. "You couldn't even get a loan at Yale Insurance, come on!"

As they entered the arena, Rory felt her stomach grumble. Nudging Glenn, "Hey, you want anything from the concession stand?"

Glenn nodded, digging some money out of his pocket. "Here. Get however many hotdogs you can with this." He patted her back, trying to manage a smile, but failing miserably.

Rory couldn't hold back the giggle, heading up the stairs. As she saw the long line, she rolled her eyes again. The show started in twenty minutes, and she knew she'd might miss some of the opening act, which was one of her new favorites, Yeah Yeah Yeahs. Crossing her arms, she was broken from her trance when she heard someone in a rough New York accent, speaking loudly behind her. "Are you kidding me? Beck couldn't hold a candle to Neil Young. Not even, not ever." The voice chuckled. "That's blasphemous."

Rory peeked behind her, finding the guy from the light post behind her, with another rather tall man standing with him. He noticed her looking, cocking an eyebrow. The other guy had noticed as well, smirking. "What do you think, dollface?"

Rory's eyes widened, shrugging. "I don't know." She turned around, not wanting to deal with anymore sketchy guys tonight. She had already felt out of her element being here, having two guys messing with her wasn't something she needed to add to her list of events this evening. As she realized the line had moved, she pulled out the wad of cash that Glenn gave, feeling someone stand beside her.

"If you're here for the Knicks game, I should tell you that you're wasting your money and that you should just go home." She knew it was the shorter, more relaxed one out of the two men, seemingly closer to her age. "But if you're here for Beck, well..." He paused, looking Rory over. "I have to say I'm surprised."

Rory had had enough of people judging her for one night, reaching her limit. "You don't even know me. I could be Beck's biggest fan for all you know. For all you know, I could have his name tattooed on butt!"

His friend laughed. "I'd love to see that."

The shorter one, threw a death glare his way, softening it toward Rory. "I didn't mean to offend you or anything, kid. Just wanted to know if you were going to be at the show."

Rory stepped up, ordering her food. "Yeah, could I have two Cokes and however many hotdogs I can get for this." She handed over the money, looking back to see the taller guy had gone, only the shorter one stood near.

"Sorry about Mack. He's kinda an asshole." He smirked again, seeing the amount of hotdogs the cashier was loading on a tray for Rory. "Hungry?"

Rory shook her head. "They're not all for me." She lifted it, regretting to volunteer to go get the food for the second or third time in the last fifteen minutes. "I better get inside."

"Let me help you at least." He reached out, as Rory handed him the tray. "My name is Jess by the way."

Rory hadn't noticed that his eyes were brown until she looked up close. She knew that she thought he wasn't hard on the eyes earlier, but with his weird approach and his friend hadn't made any good points for him. It wasn't until he gave her a small smile, nearly peeling away the tough-guy persona he had built up for his company. Rory smirked bashfully. "Thanks."

As they walked over to the entrance, Rory opened the door, taking the tray again. "I think I've got it from here." She looked up, seeing Jess openly disappointed. "Thanks again." She had turned when she felt him pull on her arm.

"Could I at least get your name? Mack's gonna break my balls, I mean, he's gonna--"

Rory smiled. "It's Rory." She budded her head, turning back toward the concert. As she went to her row, she watched Glenn meet her at the end. Passing him his food, she took a seat at the aisle, not thinking about the band that was playing, but about the smoking figure with the nonchalant smirk.

* * *

_November 2006_

Jess was polishing some glassware behind the bar, looking over the elite clientèle as they rushed back and forth from the bar to the restaurant, attempting to seem less of a mockery and more of an actual important person. The only time he liked his job was when it was empty, a few regulars at the bar whom he could serve until last call, not having to wipe behind the privileged and stand to listen to them ramble.

"Hey, Jess! We need another Gin & Tonic over here." He nodded, fixing the drink and sliding it down. Before long, another rush came, keeping him busy for another ten minutes. He liked to stay busy, but he hated the people. All the bullshit that continuously came through the door nearly gave him a nosebleed. On nights like this, he had to remember why he thought Hartford would be any slower than his fast-paced life in New York. Hartford was just another extension of New York, where all the uber rich paraded their wealth to their friends, cooped up in this little hideaway in the New England state. He would fantasized sometimes, blowing dodge and heading for the Pacific, where things were slower, steadier and he wasn't constantly bombarded by the notion that he needed to catch up or keep up.

"You alright, man? You look like shit." Russell, his manager, stepped from behind the back of the bar, with his trademark rag on his shoulder. "You wanna take a break?"

Jess shook his head, knowing that he could handle it. "I'm good, Russ." He yanked his own dishrag off his shoulder, wiping down the bar. He felt Russell pat him on the back, knowing he cared for his best interest. He had taken Jess under his wing when he had fled the bright New York lights, his mother and everything that seemed to make him feel like his drowning. It took Jess a little while to realize that around this kind, he'd always feel like he's at the deep end of the pool, desperately trying to float.

"Are you still serving?" He had his head down heard a stool squeak, smelling perfume. Another heiress, another nameless airhead. Perfect. Figuring he could keep eye contact to a minimum, he kept his head down.

Jess turned his back, grabbing a few freshly cleaned mixers. "Yeah. What can I get you?"

The woman chuckled. "Whatever's strong enough to forget tonight."

Jess finally turned around, nearly choking on his large intake of breath. He had seen beautiful women walk through from day one, even Russell telling him that if he played his cards right he could end up with not only tips but numbers from variously striking women. Jess had had a few flings here and there over the course of his year working at the restaurant, but it wasn't until seeing the woman in front of him that he was nervous being in the presence of her beauty. When she looked up, her blue eyes meeting his brown, it sealed the deal. "Um, whiskey?"

"Whatever works." She pulled out a twenty, passing it over to him. "I just want to forget."

It didn't seem melodramatic like everything most of the women drunkly stated at the bar. It seemed sincere, like she was begging for a cure for whatever turmoil seemed to spoil her evening. Jess tried to breathe through his nose, determined to not get emotionally attached to someone he barely said three words to, but there was something behind her expensive perfume, her designer duds and her elegant poise, something endearing. He fixed her up something that he knew would get her drunk in three seconds, but not enough to knock her out. "Here you go."

The woman sniffed it, scrunching up her face. "Are you trying to slip me some kind tranquilizer?" She pushed it back, crossing his arms on the bar. "Sorry, I just had a rough night."

Jess nodded, polishing another clean glass to have something to do with his hands. He kept his composure, which seemed to be harder to do as he watched her pout on the stool, clearly upset. He couldn't believe what came out of his mouth next, knowing that he would regret as soon as it left his lips. "Wanna talk about?"

The woman chuckled again, but not as pristine as before, but more like any woman that seemed to feel the sting of heartbreak. "Try being stood-up by your supposed boyfriend." She shook her head, tucking a fallen piece of hair behind her ear. "I know, I shouldn't be so upset. I mean, he was supposed to be home from London yesterday and promised me he'd be here tonight. It's just hard to trust anything he says anymore." She rolled her eyes as a small tear ran down her face. "I'm sorry. You don't care about any of this, right? I mean, I know you see me and think, 'Oh, poor little rich girl.'" She looked down at her clothes, scoffing. "Look at me. I'm a total cliché." She chuckled than, tapping the bar. "Could you fix me something that won't kill me?"

Jess blinked out of his trance, handing her a beer. "How's this?"

The woman cracked the first smile since she walked up to the bar. "Thank God, you have actual beer here. I thought I'd have to walk down to the liquor down the street to get anything good." She took a swig, smirking. "Thank you."

Jess smirked. "You're welcome." He tried to break away from her, seeing a few people queuing up. He shrugged at her, seeing her nod at acknowledgement. After serving the others, he made his way back to the end of the bar, where she had nearly finished her bottle. "Want another?"

"Of course." She pulled another twenty out when Jess shook his head. Smirking, she nodded. "Thanks." She took the bottle from him, smiling again. "Rory." She extended her hand, chuckling as Jess seemed to recoil at it.

He never had anyone actually want to introduce themselves to him other than the local drunks that wanted everyone to be their friends. He shook it than, allowing a smile to reach his lips. "Jess."

"Nice to meet you." She continued to sip her beer, looking around. "I go to Yale. You know, the university?"

Jess nodded vaguely, figuring she went there or another Ivy League school that only seemed to open for students with Daddy's good name and unlimited trust funds. "Good school."

Rory chuckled. "Best school in the whole world." She took another swig, slamming the bottle down. "I love it so much. I mean, I had wanted to go to Harvard since I was like three or something, but Yale... I don't know, it just seemed better. I never really considered it until like the very end." She shook her head. "Funny how life can be sometimes, huh?"

Jess looked up, trying to figure out what she was trying to say. "How's that?"

Rory shrugged. "You know, how you think you're life can go one way and than something happens and changes everything. I mean, I had my heart on some many things, people that I trust... and sometimes things change. People change." She looked up again, seeing Jess looked alarmed. "I'm sorry, I really shouldn't be talking this much." She finished her beer, shaking her head. "I'm just gonna sit here until I sober up." She sat up higher, blinking her eyes. "I'm fine, don't worry about me."

Jess sighed, crossing his arms. "Could I give you some advice?" He wasn't sure what would follow that, but he felt it was something he needed to ask.

Rory turned to him, smirking. "Sure." She smiled, "It must be nice to be able to dispel your wisdom on us poor drunkards." She shook her head. "Sorry, forget I said that."

Jess shrugged. "It's okay. I mean, I'm kinda a cliché myself." He leaned over, watching leaned closer as well. "You should just relax. You seem kinda tense."

"Relax?" Rory snorted. "That's your advice?!" She shook her head. "Great."

"I'm serious. You can't always plan everything. You just have to go with the flow." Jess took her beer bottles, wiping down the bar. "At least than you'll won't be disappointed."

Rory nodded than, letting another smile reach the surface. "I suppose you're right." She watched Jess as he wiped some more glasses, leaning over. "Thanks." She leaned back, meeting his eyes again.

Jess felt another lump in his throat form, shocked by his own lack of resistance to her beauty. However, he didn't notice the blond walking down the steps down to the bar, heading for the bar. "Ace!"

Rory turned, smiling. "Logan!" The blond came down, pulling her off the stool and hugging her in one fluid motion. He kissed her cheek, placing his hand on the small of her back. "I'm sorry I'm late. I couldn't leave the office and than I left my cell at this other--"

"It's okay." Rory budded toward the restaurant. "I'll be over there in a moment." She watched Logan walk away, turning back to Jess who watched the entire exchange. "I guess I overreacted."

Jess simply grunted, not looking up again. "I guess you did." He chuckled. "I told you to relax."

Rory nodded. "Yeah, I'll keep that in mind." She reached out to him than, laying a gentle hand on his. "Thanks for the beers." With another smile, she turned to join her boyfriend, leaving Jess speechless.

Jess took another breath, stepping away from the bar. "Hey Russ, I'm gonna take that break now!"

* * *

_February 2008_

Jess was scratching his head, pushing his coffee across the table. "Who the hell are you telling me about, Chris?"

"Barack Obama, man. The next president of these here United States." Chris scoffed. "You read all the great literary works in the world, but you don't even know what's going on right here in your own country."

"Bush is an asshole. I think I know enough." Jess chuckled as Chris rolled his eyes.

"True, but that's not all of it." He pulled at a flyer, passing it across the table. "This guy, here, Barack Obama, he's about something, man. He's not for all the 'good 'ol boy' bullshit of yesteryear. He's about the people, about this country. He's real, man."

Jess picked up it up, nodding. "So he's gonna down at NYU today?"

"And so are we. We have to hear this guy, mostly you, dude." Chris took back the flyer, folding it and putting it back in his pocket. "He's actually gonna be there in about an hour, so we better get going if we're gonna get a good spot." He stood up than, waiting for Jess to join him. "Come on, man. Just give him a chance."

Jess rolled his eyes, walking toward the door. "Let's get this over with."

Jess and Chris walked up to the quad, seeing hundreds crowding around the makeshift stage that was displayed near the front. Chris pulled Jess along. "I just got a text from Lucas. He's near the front, come on." He pulled Jess through the crowd, finding their mutual friend.

"What's up, man?" Jess shook his head, pulling a cigarette from behind his ear. "Are you all gun-hoe for this guy too?" As he lit it, he looked around, seeing posters and banners, displaying the name: "Obama".

"Hell yes. He's gonna be the next president, mark my words." Lucas opened his jacket, revealing a shirt that read: "Barack the Vote". "See man, even his name is awesome." He chuckled. "But seriously, have you read about his policies. He wants to actually do something for the middle class."

Jess rolled his eyes. "Here we go." He shook his head. "I'm here to keep an open mind." He stifled a chuckle. "I'm still undecided being an independent an all." He watched his two friends with their gaped mouths. "I'm still considering Hilary Clinton, she is our Senator."

Chris nudged Jess. "At least you're voting Democratic."

Jess shrugged. "Than again, I could always vote for McCain." He laughed than, being pummeled by his friends. He noticed a coffee stand nearby, walking toward. "Be right back." He drew closer, seeing someone step in line before him.

"Two, please." The woman in front of him turned toward the stage. She wore a large Obama pen on her lapel of her coat, smiling widely. "Don't you love the smell of politics?"

"It has a smell?" Jess shrugged, ordering himself a coffee. "I guess if you're into that ripe 'old man' smell." He noticed the woman chuckle, feeling relieved. "I take it you're a supporter for him, huh?"

She nodded. "Yeah, I'm actually working on his campaign." She shrugged. "We thought it would be a smaller turnout since this is the home state for Clinton, but I'm really impressed." She smiled again, making a starry-eyed glance toward the stage where more people were setting up. "He's gonna change the world, you know?"

Jess rolled his eyes. "I don't get all the fascination with this guy. I mean, I heard a few things, but he's not the second coming of Christ or anything."

The woman glared at him than. "I never said that. All I ever said was that he seemed to have a real eye for change, not the kind of change like addresses or breaking change for the rich. I mean, he's going to change the way people think about American politics."

Jess nodded, not wanting to upset her again. Truth be told, he thought her little speech was pretty cute, even though she seemed completely sincere, which only made it that more endearing. "Do you want to be a politician too?"

The woman shook her head. "Oh no, I want to be a journalist." She said it so refined like she had said it her entire life. "And he's given me my chance. I owe him a lot."

"Including your vote?" Jess couldn't understand someone with such determination to make her point. "I think that should be up to his own merits, not what he's done for you."

The woman rolled her eyes in frustration again. "Stop twisting my words." She sighed. "Look, Mr. Green Party Pete, I'm not supporting him because he gave me a break. I'm voting for him because he's going to give a country a break. He's going to make it possible to actually achieve the American dream again. It won't only be reserved for the rich anymore."

Jess chuckled than. "'Green Party Pete', huh?" He took a sip of his coffee. "It's actually Jess." He watched the woman nod again, looking back at the stage.

"Rory." She stiffened slightly, trying to avoid his eyes.

"Nice to talk to you." He looked her over again, not disregarding that she was extremely pretty, nearly too pretty to be standing so close to him. He moved than, feeling uncomfortable. "I better get back to my friends."

Rory looked up, seemingly disappointed. "Oh, okay." She extended her hand. "Thanks for talking with me and I hope you make the right decision come November." She managed a smile, making it impossible for her not to seem anything less than perfect.

Jess shook her hand, allowing a smile. "I'll keep that in mind." He waved so long, walking back to meet his friends and as he watched the lean black politician approach the stage to a round of cheer and applause, he couldn't help but think that in November, he'd be voting for Rory, not Obama.

* * *

_September 2009_

"I can't believe you're actually making go through with this." Rory went scrambling around her apartment, looking for her other shoe. "Where did I put--"

"Looking for this?" Her roommate handed her other boot, chuckling. "I swear, you'd forget your head if you didn't need so much." She plopped on the couch. "And you're going because you haven't seen anyone since Spencer, and that was six months ago."

"First of all, Meagan, I've seen other people after him." She stuffed her foot into the boot, looking round for her cardigan sweater. "Second of all, I don't remember agreeing to a blind date."

Meagan chuckled. "Well, it doesn't matter because you're going. And Rachael knows him. She said he's really cute. And he likes to read."

Rory perked up than. "I'm going, alright." She grabbed her jacket and walking toward the door. "If it's a total disaster, I'm blaming both you and Rachael." Slamming the door, she rolled her eyes at the prospective suitor her "friends" set her up with.

--------

"This is stupid. You do realize, this?" Jess walked around his kitchen, looking for his watch. "A Yale grad? What the hell could we possibly have in common?"

"You'd be surprised. Rachael said she's a small town girl. You know, she has actual family values and stuff." His friend propped his feet on the coffee table.

"The more reason why we have nothing in common. Geez." He grabbed his jacket, feeling inadequate. "Mark, have you seen my watch?"

Mark walked across the floor, handing it to him. He patted Jess on his back, managing a smile. "She seems like a cool chick, man. And besides, if it doesn't work out with you two, I have no problem taking her off your hands." He nudged him, getting a rise out of Jess. "You'll be fine, man."

"I suppose." He nodded at his reflection, grabbing a book and stuffing it in his back pocket and his glasses on the small table by the door. "Later!"

-------

Rory looked at her watch, seeing she was a few minutes late. "Crap." She walked faster, turning as she see saw the coffee house up the street. She opened the door, scanning the room. It wasn't until her eyes fell on a man, reading a Hemingway novel that she figured that was her date. "Perfect, he likes Hemingway." She wanted to turned and leave than when he looked up. An involuntary smile crossed her face, finding her limbs walking toward him. "Jess?"

Jess stood up, nodding. "Rory?" When Rory nodded, he put his book back in his pocket. He noticed her watching his book. "You like Hemingway?"

Rory rolled her eyes. "As much as I like root canals." She chuckled than. "He's alright. I'm more of a Richard Yates kind of girl."

Jess motioned for her to sit across from him, allowing a smile on his lips. "Yates is okay." He crossed his arms. "Willing to change my mind?"

Rory chuckled, crossing her arms to reflect his stance. "Willing to change my mind on Hemingway?"

Jess nodded slowly, motioning for a server. "I think we'd better get a few coffees in us first. It might be a long night."

* * *

**FIN.**

_A/N: This will not continue. Thanks so much for reading. Cheers!_


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